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Previous issue date: 2003-11-18 / Universidade Federal de Sao Carlos / This
work describes the phytochemical study of two plant species Galipea bracteata and
Ravenia infelix belonging to the family Rutaceae, aiming the isolation and structure
determination of componds from leaves and branches of these plants. This work is
also directed to the search of trypanocidal and leishmanicidal compounds from these
plants. The following models were used to check the biological activities of the
isolated compounds: antiparasitc activity - trypomastigote form of Trypanosoma cruzi
in vitro , enzymatic inhibitory activity on gGAPDH (Glyceraldeyde 3- phosphate
dehidrogenase) of T. cruzi and enzymatic inhibitory activity on APRT (Adheninephosphoribosyl-
transferase) of Leishmania tarentolae. The leaves extract of G.
bracteata afforded tirtheen quinoline alkaloids. Among these compounds seven have
been described for the first time: 2-(3 ,4 -methylenedioxyphenylethyl)quinoline, 4-
methoxy-2-(propan-1 -ona)quinoline (inedit), 4-methoxy-2-(1 ,2 -transepoxypentyl)
quinoline (inedit), 4-methoxy-2-n-heptylquinoline, 2-(1 ,2 -transepoxypentyl)
quinoline (inedit), 4-methoxy-2-(3 ,4 -
methylenedioxyphenylethyl)quinoline, 4-methoxy-2-(1 ,2 -trans-epoxypropyl)quinoline
(inedit), 4-methoxy-2-n-propylquinoline, 2-n-pentylquinoline, 2-(propan-1 -
one)quinoline (inedit), 4-methoxy-2-(pentan-1 -one)quinoline (inedit), 2-(pentan-1 -
one)quinoline (inedit), a mixture of steroids campesterol, stigmasterol and sitosterol,
one furoquinoline alkaloid evolitrine, a mixture of seco-furoquinoline alkaloids Edimethylrhoifolinate
and Z-dimethylrhoifolinate, a pentacylclic triterpene arborinol and
norsesquiterpene 3,5-dihydromegastigma-6,7-diene-9-one. From the branches of R.
Infelix were isolated the carbazole alkaloids: 3-methylcarbazole and girinimbin, the
steroids: 7-oxo-stigmasterol and 7-oxo-sitosterol, the indol 3-carboxaldeheide and
mixtures of amides: N-trans and N-cis-feruloyltyramine, and N-trans and-cis-pcumaroyltyramine.
The pure compounds had their trypanocidal and leishmanicidal
activities determined. / O presente
trabalho descreve o estudo fitoquímico de duas espécies de plantas pertencentes à
família Rutaceae, no intuito de elucidar estruturas de micromoléculas presentes nas
folhas e galhos. O estudo de Galipea bracteata e Ravenia infelix (Rutaceae) está
também associado à busca de metabólitos com atividades tripanocida e
leishmanicida, através dos seguintes modelos experimentais selecionados para
verificação da atividade biológica: atividade antiparasitária forma tripomastigota de
Trypanosoma cruzi in vitro , inibição enzimática in vitro (gGAPDH - Gliceraldeído-
3-fosfato-desidrogenase de T. cruzi) e inibição enzimática in vitro (APRT
Adenina-fosforribosil-transferase de Leishmania tarantolae). Dos extratos das folhas
de Galipea bracteata foram isolados treze alcalóides quinolínicos, dentre estas
substâncias sete estão sendo descritas pela primeira vez: 2-(3 ,4 -
metilenodioxifeniletil)quinolina, 4-metoxi-2-(propan-1 -ona)quinolina (inédita), 4-
metoxi-2-(1 ,2 -trans-epoxipentil)quinolina (inédita), 4-metoxi-2-n-pentilquinolina,
4-metoxi-2-n-heptilquinolina, 2-(1 ,2 -trans-epoxipentil)quinolina (inédita), 4-metoxi-2-
(3 ,4 -metilenodioxifeniletil)quinolina, 4-metoxi-2-(1 ,2 -trans-epoxipropil)quinolina
(inédita), 4-metoxi-2-n-propilquinolina, 2-n-pentilquinolina, 2-(propan-1 -
ona)quinolina (inédita), 4-metoxi-2-(pentan-1 -ona)quinolina (inédita), 2-(pentan-1 -
ona)quinolina (inédita), mistura dos esteróides campesterol, estigmasterol e β-
sitosterol, um alcalóide furoquinolínico evolitrina, uma mistura de alcalóides seco
furoquinolínicos E e Z-rhoifolinato de dimetila, o triterpeno pentacíclico arborinol e o
norsesquiterpeno 3,5-diidromegastigma-6,7-dieno-9-ona. Dos galhos de R. infelix
foram isolados os alcalóides carbazóis: 3-metilcarbazol e girinimbina, os esteróides:
7-oxo-estigmasterol e 7-oxo-β-sitosterol, o indol: indol-3-carboxaldeído e misturas
das amidas N-trans e N-cis-feruloiltiramina e N-trans-p e N-cis-p-cumaroiltiramina.
Estas substâncias puras foram submetidas a testes para verificação das atividades
tripanocida e leishmanicida.
| Identifer | oai:union.ndltd.org:IBICT/oai:repositorio.ufscar.br:ufscar/6368 |
| Date | 18 November 2003 |
| Creators | Andrade, Márcio Roberto de |
| Contributors | Vieira, Paulo Cezar |
| Publisher | Universidade Federal de São Carlos, Programa de Pós-graduação em Química, UFSCar, BR |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | Portuguese |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis |
| Format | application/pdf |
| Source | reponame:Repositório Institucional da UFSCAR, instname:Universidade Federal de São Carlos, instacron:UFSCAR |
| Rights | info:eu-repo/semantics/openAccess |
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